144302-38-5Relevant academic research and scientific papers
Chemoselective and stereoselective synthesis of gem-difluoro-β-aminoesters or gem-difluoro-β-lactams from ethylbromodifluoroacetate and imines during Reformatsky reaction
Boyer, Nicolas,Gloanec, Philippe,De Nanteuil, Guillaume,Jubault, Philippe,Quirion, Jean-Charles
, p. 12352 - 12366 (2008/03/12)
The chemoselective and stereoselective synthesis of gem-difluoro-β-aminoesters or gem-difluoro-β-lactams was investigated from ethylbromodifluoroacetate and imines during Reformatsky reaction. Influence of various reaction parameters, such as nature of the amine part, nature of the chiral auxiliary, was evaluated. High levels of stereoselectivity (up to 98%) were obtained for gem-difluoro-β-aminoesters and gem-difluoro-β-lactams using either (R)-phenylglycinol or (R)-methoxyphenylglycinol.
Diastereoselective addition of silyl enol ether to chiral imines and 1,3-oxazolidines using a Lewis acid
Higashiyama, Kimio,Kyo, Hideyoshi,Takahashi, Hiroshi
, p. 489 - 490 (2007/10/03)
The Lewis acid promoted reaction of silyl enol ether to chiral imines and 1,3-oxazolidines derived from (R)-phenylglycinol afforded with good diastereoselectivity the (R,R)-β-amino ester derivatives from the imines, and the (R,S)-β-amino ester derivatives from the 1,3-oxazolidines.
Enantioselective synthesis of diverse α-amino phosphonate diesters
Smith III, Amos B.,Yager, Kraig M.,Taylor, Carol M.
, p. 10879 - 10888 (2007/10/03)
An efficient, versatile protocol for the synthesis of highly enantioenriched α-amino phosphonate diesters has been devised. Addition of lithium diethyl phosphite to chiral chelating imines 31a-j, prepared from a variety of aldehydes and the chiral auxilia
Reversal of Diastereofacial Selectivity in the Addition Reaction of Organometallics to Chiral Imines
Ukaji, Yutaka,Watai, Toshiyuki,Sumi, Takashi,Fujisawa, Tamotsu
, p. 1555 - 1558 (2007/10/02)
It was observed that diastereofacial selectivity in the addition reaction of organometallics to the chiral imines derived from (R)-2-methoxy-1-phenylethylamine was regulated under appropriate conditions; i. e., organolithium and organocerium reagents added from the re-face of the chiral imines selectively, while organocopper reagents attacked from the si-face.The utility of the present method was demonstrated in the enantioselective synthesis of solenopsin A.
